- Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules
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A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.
- Kumar, Vasantha,Rai, Vaishali M.,Udupi, Vishwanatha,Shivalingegowda, Naveen,Pai, Vinitha R.,Krishnappagowda, Lokanath Neratur,Poojary, Boja
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p. 793 - 808
(2021/08/12)
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- Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents
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Several classes of antimalarial drugs are currently available, although issues of toxicity and the emergence of drug resistant malaria parasites have reduced their overall therapeutic efficiency. Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated for in vitro antiplasmodial activity against the 3D7 chloroquine-sensitive strain of Plasmodium falciparum, and compounds 40 and 59 emerged as the most promising with IC50 values of 0.23 and 0.93 μM, respectively. The most promising compounds were also evaluated in silico by molecular docking protocols for binding affinity to the {0 0 1} fast-growing face of a hemozoin crystal model.
- Bokosi, Fostino R.B.,Beteck, Richard M.,Mbaba, Mziyanda,Mtshare, Thanduxolo E.,Laming, Dustin,Hoppe, Heinrich C.,Khanye, Setshaba D.
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- Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents
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A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 μM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.
- Insuasty, Daniel,García, Stephanie,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Borosky, Gabriela L.,Laali, Kenneth K.
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- Synthesis and characterization of biologically important quinoline incorporated triazole derivatives
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Triazoles are well recognized in literature for their significant biologically active heterocyclic compounds. Also the quinoline nucleus found in several natural products shows a varied biological activity. Keeping in the view of these observations, a novel series of 6/7/8-substtuted-2-[(5-((4-chlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio]quinoline-3-carbaldehydes and 6/7/8-substituted-2-[(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio]quinoline-carbaldehydes were synthesized by the condensation of 5-(4-chloro phenoxy methyl)-2,4-dihydro-1,2,4-triazole-3-thiones and 5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiols with 6/7/8-substituted-2-chloro quinoline-3-carbaldehydes. The new series were established by Mass, NMR and IR spectroscopy and were also screened for their antimicrobial activities. A few of the novel compounds exhibited tremendous bioactivities compared to that of normal drug.
- D'Souza, Vineetha Telma,Nayak, Janardhana,D'Mello, Desmond Edward,Dayananda
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- Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition
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Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones 8j-v were synthesized by click chemistry as an ultimate tactic where [3 + 2] cycloaddition of azides with terminal alkynes has been evolved. Herein, we are inclined to divulge the implication and prevalence of CuSO4·5H2O and THF/water promoted [3 + 2] cycloaddition reactions. The foremost supremacy of this method are transitory reaction times, facile workup, excellent yields (88–92%) with exorbitant purity and regioselective single product formation both under conventional and microwave method. Docking studies illustrated strong binding interactions with enzyme InhA-D148G (PDB ID: 4DQU) by means of high C-score values. The anti-tubercular and antifungal screening of synthesized compounds proclaimed promising activity. The in vitro and in silico studies imply that these triazoles appended quinolines may acquire the ideal structural prerequisites for auxiliary expansion of novel therapeutic agents.
- Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Shaikh, Saba Kauser J.,Hoolageri, Swati R.,Kodasi, Barnabas,Joshi, Shrinivas D.,Kumbar, Vijay M.
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supporting information
(2021/04/12)
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- Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-: B] quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones
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An enantioselective synthesis of highly functionalized 1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3-b]quinolines from modified MBH carbonates and pyrazolones via a chiral phosphine-mediated alkylation/annulation sequence has been realized. The chiral dihydropyrano[2,3-c]pyrazoles bearing bio-active condensed heterocycles were facilely formed in good chemical yields and with high to excellent enantioselectivity by utilizing low catalyst loading.
- Li, Jingyi,Ling, Fei,Lu, Yin-Jie,Shao, Bingxuan,Xiao, Xiao,Yang, Zehui,Zhong, Weihui
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supporting information
p. 4690 - 4693
(2021/05/19)
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- Synthesis, in silico Molecular Docking and Antimicrobial Study of Some New 3-(Substituted-quinolin-3-yl)-1-[4-(1H-pyrrol-1-yl)phenyl]prop-2-en-1-one Derivatives
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New series of 3-(substituted-2-chloroquinolin-3-yl)-1-(4-(1H-pyrrol-1-yl)phenyl)prop-2-en-1-ones 4(a-e)/3-(substituted-2-methoxyquinolin-3-yl)-1-(4-(1H-pyrrol-1-yl)phenyl)prop-2-en-1-ones 6(a-e) were synthesized by base catalyzed reaction/chalcone synthes
- Almehizia, Abdulrahman A.,Alshabi, Ali Mohamed,Joshi, Shrinivas D.,Kulkarni, Venkatarao H.,Kumar, R. Prem,Shaikh, Ibrahim Ahmed
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- Synthesis and antimicrobial activities of thiadiazole containing quinoline derivatives
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A novel series of 1-[(substituted 2-chloroquinolin-3-yl)methylidene]-3-[substituted-5-phenyl-1,3,4-thiadiazol-2-yl] thioureas have been synthesized by acid catalyzed reaction between the 1-(5-substitued phenyl-1,3,4-thiadiazol-2-yl) thioureas and 6-substi
- Dayananda,Nayak, Janardhana,D'Souza, Vineetha Telma
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p. 633 - 638
(2021/09/28)
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- Synthesis, photophysical properties and theoretical studies of new bis-quinolin curcuminoid BF2-complexes and their decomplexed derivatives
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This paper presents the synthesis and characterization of two series of new bis-quinolin curcuminoid BF2-complexes 11 and their respective decomplexed bis-quinolin curcuminoid derivatives 12, in an attempt to understand their optical properties. The synthesized compounds showed interesting fluorescent characteristics in both solution and in solid-state. The characteristic of the electronic transitions involved in these systems were measured via Uv-vis spectroscopy and fluorescence spectroscopy. Results revealed that the absorption and emission bands are dependent of the structure of compounds 11 and 12 but also of the type of substituent, even showing a push-pull behavior in those derivatives substituted with methyl group. These findings were also confirmed through computational calculations at DFT level via simulations of the Uv-vis spectra and determining the topology of the border orbitals responsible for light absorption.
- Abonia, Rodrigo,Cabrera, Lorena,Insuasty, Braulio,Insuasty, Daniel,Ortiz, Alejandro,Quiroga, Jairo
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- Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones
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Fifteen 2-quinolone thiosemicarbazone derivatives of which eleven were new, were synthesized at room temperature. The key intermediate was the quinolone carbaldehyde, from which thiosemicarbazones were formed by the reaction of thiosemicarbazides with the aldehyde moiety. The structures of the synthesized compounds were elucidated by 1D and 2D-NMR spectroscopy and mass spectrometry. The synthesized compounds showed antibacterial activity with MBCs in the range 0.80 to 36.49 mM against Staphylococcus aureus, Staphylococcus aureus Rosenbach (MRSA), Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Salmonella typhimurium. The best activity was seen when a larger halogen such as chlorine and bromine were substituted at C-6 on the quinolone scaffold and when a planar phenyl group was present on the thiosemicarbazone moiety. Activity was reduced when a smaller fluorine atom was present at C-6 or when a methyl group was attached to the thiosemicarbazone. This group of compounds showed a high negative binding affinity, which suggested promising antimcrobial activity. The 6-chloro derivative with a phenyl group on the thiosemicarbazone had the greatest negative binding affinity.
- Govender, Hogantharanni,Mocktar, Chunderika,Kumalo, Hezekiel M.,Koorbanally, Neil A.
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p. 1074 - 1081
(2019/06/10)
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- Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
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A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH(Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.
- Abonia, Rodrigo,Gutiérrez, Luisa F.,Insuasty, Braulio,Quiroga, Jairo,Laali, Kenneth K.,Zhao, Chunqing,Borosky, Gabriela L.,Horwitz, Samantha M.,Bunge, Scott D.
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p. 642 - 654
(2019/04/17)
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- Synthesis and Bioactivity of Quinoline-3-carboxamide Derivatives
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Twelve novel substituted 2-chloroquinoline-3-carboxamide derivatives were prepared from acetanilides using the Vilsmeier–Haack reaction, producing 2-chloro-3-carbaldehyde quinolines, followed by oxidation of the 3-carbaldehyde to the carboxylic acid and coupling this group with various anilines. The structures of the synthesized compounds were confirmed by NMR, mass spectrometry, and single crystal X-ray diffraction. The chemical shifts of H-5 and H-8 were shown to be influenced by the substituent at C-6. The substituent at C-6 was also seen to affect the chemical shift of C-5, C-7, and C-8, with C-5 and C-7 being more shielded in 5j (F substituted) in comparison with 5g (Cl substituted) and 5d (CH3 substituted). The compounds showed weak activity in the mM range against Gram-positive and Gram-negative bacteria of which 5b, 5d, and 5f showed the best activity with minimum bactericidal concentration values for 5b being 3.79?mM against methicillin-resistant Staphylococcus aureus and 5d and 5f having minimum bactericidal concentration values of 3.77 and 1.79?mM against S.?aureus ATCC 25923, respectively.
- Govender, Hogantharanni,Mocktar, Chunderika,Koorbanally, Neil A.
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p. 1002 - 1009
(2018/02/15)
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- Microwave-assisted synthesis of diversely substituted quinoline-based dihydropyridopyrimidine and dihydropyrazolopyridine hybrids
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An efficient, catalyst-free, and one-pot three-component procedure for the synthesis of novel and nitrogen rich dihydropyrido[2, 3-d]pyrimidines and dihydro-1H-pyrazolo[3, 4-b]pyridines bearing a quinoline pharmacophore fragment is provided. Reactions proceeded in DMF under microwave irradiation of three-component mixtures of formyl-quinoline derivatives, primary heterocyclic amines and cyclic 1, 3-diketones. Interestingly, when conventional heating at reflux was used for the starting 5-amino-1-phenylpyrazole, the corresponding aromatized pyrazolopyridines were obtained as the main products. Single crystal X-ray analysis confirmed unequivocally the structure of both the dihydro- and aromatized products.
- Insuasty, Daniel,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Laali, Kenneth K.,Nogueras, Manuel,Cobo, Justo
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supporting information
p. 555 - 563
(2017/10/13)
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- A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents
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Novel tetrahydro-5H-benzo[e][1,4]diazepin-5-ones, several of them, containing the quinoline pharmacophore, were synthesized via a Schmidt rearrangement from their corresponding 1,2,3,4-tetrahydro-4-quinolones mediated by the NaN3/H2SO4 reaction conditions. Twelve of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where compound 24a presented a remarkable activity against 58 of the 60 cancer cell lines, with the most important GI50 values ranging from 0.047 to 8.16 μM and LC50 values ranging from 9.4 to > 100 μM. Additionally, some of them were evaluated as antimalarial, antitrypanosomal and antileishmanial agents. The best antimalarial response was observed for compound 22g with an EC50 = 13.61 μg/mL for Plasmodium falciparum, while compound 24d exhibited high activity against Trypanosoma cruzi. and Leishmania (V) panamensis with EC50 = 2.78 μg/mL and 3.35 μg/mL respectively.
- Insuasty, Daniel,Robledo, Sara M.,Vélez, Iván D.,Cuervo, Paola,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Abonia, Rodrigo
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p. 567 - 583
(2017/11/03)
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- Synthesis and antimicrobial activity of azetidin-2-one fused 2-chloro-3-formyl quinoline derivatives
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Azetidin-2-one fused 2-chloro-3-formyl quinolines derivatives, 3-chloro-4-(2-chloro-8/7/6-methoxyquinolin-3-yl)-1-(2,4-dinitro/4-nitro phenylamino)azetidin-2-one,3-chloro-4-(2-chloro-8/7/6-chloroquinolin-3-yl)-1-(2,4-dinitro/4-nitro phenylamino)azetidin-2-one, 3-chloro-4-(2-chloro-8/7/6-methylquinolin-3-yl)-1-(2,4-dinitro/4-nitrophenylamino) azetidin-2-one were synthesized by four steps, respectively from N-arylacetamides, 2-chloro-3-formyl quinolines, 2,4-dinitro/4-nitro phenyl hydrazine reflux with chloroacetyl chloride and triethyl amine. However yields of quinolines having electron donating groups in all cases. The structures of the synthesized compounds have been established on the basis of physical and spectral data. The antibacterial and antifungal activity of these compounds was tested by filter paper disc method against Staphylococcus aureus (MTCC96), Escherichia coli (MTCC722) and Candida albicans (MTCC183). The results showed that azetidin-2-one fused 2-chloro-3-formyl quinolines derivatives are better in inhibiting the growth of both types of organisms. Compounds AZT b2, AZT b3 to AZT g2, AZT g3 were found to be more potent compared to standard drug.
- Nayak, Govind,Shrivastava, Birendra,Singhai, Akhlesh Kumar
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p. 1977 - 1982
(2016/10/24)
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- 2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier-Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides
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TCTA-DMF (2,4,6-trichloro-1,3,5-triazine/N,N′-dimethylformamide) adduct has been used as a Vilsmeier-Haack type reagent for effective synthesis of 2-chloro-3-formyl quinolines from acetanilides under conventional and ultrasonically assisted conditions. The reaction times under sonication are quite significantly shorter than conventional methods even though the yields obtained under sonication are comparable with those obtained under reflux conditions.
- Venkanna,Rajanna,Satish Kumar,Bismillah Ansari, Mohd.,Moazzam Ali
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supporting information
p. 5164 - 5167
(2015/08/19)
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- Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
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4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure-activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-l, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (Ki = 0.009 ~M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-l was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.
- Wang, Da-Wei,Lin, Hong-Yan,Cao, Run-Jie,Chen, Tao,Wu, Feng-Xu,Hao, Ge-Fei,Chen, Qiong,Yang, Wen-Chao,Yang, Guang-Fu
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p. 5587 - 5596
(2015/06/25)
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- Synthesis and anticancer activity of novel curcumin-quinolone hybrids
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A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase.
- Raghavan, Saiharish,Manogaran, Prasath,Gadepalli Narasimha, Krishna Kumari,Kalpattu Kuppusami, Balasubramanian,Mariyappan, Palanivelu,Gopalakrishnan, Anjana,Venkatraman, Ganesh
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p. 3601 - 3605
(2015/08/11)
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- Design, synthesis of quinolinyl Schiff bases and azetidinones as enoyl ACP-reductase inhibitors
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New series of quinoline derivatives were synthesized from 2-chloroquinoline-3-carbaldehydes. In the reaction sequence, substituted acetanilides were cyclized to give 2-chloroquinoline-3-carbaldehydes 2a-d, which were transformed to 6a-d, which were then c
- Joshi, Shrinivas D.,More, Uttam A.,Parkale, Deepak,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Jawarkar, Rahul
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p. 3892 - 3911
(2015/10/06)
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- Synthesis of new 3-(2-Chloroquinolin-3-yl)-5-phenylisoxazole derivatives via click chemistry approach
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Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3- yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline- 3-carbaldehyde (2a-j) and phenylacetylene. Finally these derivatives were screened for their antibacterial evaluation in vitro against three Gram-negative clinical bacteria: Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii using standard methods.
- Ferna?ndez-Galleguillos, Carlos,Saavedra, Luis A.,Gutierrez, Margarita
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p. 365 - 371
(2014/02/14)
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- Microwave assisted one pot synthesis of some pyrazole derivatives as a safer anti-inflammatory and analgesic agents
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A series of pyrazolo[3,4-b]quinolines have been synthesized using one-pot water mediated synthetic route under microwave irradiation involving the condensation of 2-chloroquinoline-3-carbaldehydes with semicarbazide or 2,4-dinitrophenyl hydrazine. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation actions. The pharmacological evaluation showed that the compounds are good at inhibiting edema induced by carrageenan and also showed prominent analgesic activity with lesser GI toxicity as indicated by severity index and LPO values.
- Alam, Mohammad Mumtaz,Marella, Akranth,Akhtar, Mymoona,Husain, Asif,Yar, Mohammad Shahar,Shaquiquzzaman, Mohammad,Tanwar, Om Prakash,Saha, Rikta,Khanna, Suruchi,Shafi, Syed
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p. 435 - 441
(2013/07/28)
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- The design, synthesis and antimicrobial activity of new biquinoline derivatives
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A simple and efficient method has been developed for the synthesis of some novel biquinoline derivatives bearing a thiazole moiety through a onepot three-component condensation of 2-chloro-3-formylquinolines, ethyl cyanoacetate and a β-enaminone using a catalytic amount of piperidine in refluxing ethanol. These molecules were evaluated in vitro for their antibacterial and antifungal activity. Most of the compounds exhibited moderate antibacterial and antifungal activity against all the tested strains.
- Shah, Nirav K.,Shah, Nimesh M.,Patel, Manish P.,Patel, Ranjan G.
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scheme or table
p. 279 - 286
(2012/06/01)
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- Synthesis, characterization and antimicrobial activity of some new biquinoline derivatives containing a thiazole moiety
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A series of new biquinoline derivatives containing a thiazole moiety were synthesized by a one-pot, base-catalyzed cyclocondensation reaction of 2-chloro-3-formyl quinoline, malononitrile and enaminone. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR data. All the synthesized compounds were screened against three bacterial pathogens, namely Bacillus cereus, B. substilis and Escherichia coli and for antifungal activity against three fungal pathogens, Aspergillus niger, Fusarium oxisporum and Rhizopus using the disc diffusion method.. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
- Shah, Nirav K.,Shah, Nimesh M.,Patel, Manish P.,Patel, Ranjan G.
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scheme or table
p. 454 - 457
(2012/06/01)
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- Zn(OTf)2-catalyzed three component, one-pot cyclocondensation reaction of some new octahydroquinazolinone derivatives and access their bio-potential
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An efficient synthesis of some new octahydroquinazolinone derivatives 4a-x by the cyclocondensation reaction of corresponding 2-thi(oxo)-1,2- dihydroquinoline-3-carbaldehyde 1a-e, 1,3-dicarbonyl compounds 2a-b, and substituted urea 3a-c using zinc triflat
- Shah, Pushpak M.,Patel, Manish P.
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experimental part
p. 1188 - 1198
(2012/08/08)
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- Synthesis of a novel class of some biquinoline pyridine hybrids via one-pot, three-component reaction and their antimicrobial activity
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A small library of novel class of biquinoline containing pyridine moiety were synthesized by a one-pot cyclocondensation of 2-chloro-3-formyl quinoline, active methylene compounds and 3-(pyridine-3- ylamino)cyclohex-2-enone in the presence of catalytic am
- Shah, Nimesh M.,Patel, Manish P.,Patel, Ranjan G.
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body text
p. 669 - 677
(2012/09/07)
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- New N-arylamino biquinoline derivatives: Synthesis, antimicrobial, antituberculosis, and antimalarial evaluation
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A new series of N-arylamino biquinoline derivatives 5a-x were synthesized by reaction of 2-chloro-3-formyl quinolines 2a-d with malononitrile and various enhydrazinoketones 4a-f in absolute ethanol. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against a representative panel of pathogenic strains and antituberculosis activity against Mycobacterium tuberculosis H37Rv. Compounds 5h and 5s exhibited excellent antibacterial activity and some of the compounds demonstrated moderate antituberculosis activities compared with the first line drugs. The compounds were evaluated in vitro for their activity against the growth of Plasmodium falciparum, the malaria causing parasite. Some of them showed antimalarial activity with IC50 values as low as 0.005-0.009 μg/mL.
- Shah, Nimesh M.,Patel, Manish P.,Patel, Ranjan G.
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scheme or table
p. 239 - 247
(2012/09/08)
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- Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]-quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents
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A series of some new tetrazolo[1,5-a]quinoline based tetrasubstituted imidazole derivatives 6a-l have been synthesized by a reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde 3a-d, benzil 4, aromatic amine 5a-c and ammonium acetate in the presence of io
- Mungra, Divyesh C.,Kathrotiya, Harshad G.,Ladani, Niraj K.,Patel, Manish P.,Patel, Ranjan G.
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p. 1367 - 1370
(2013/02/25)
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- Search for new pharmacophore as antimalarial agent: Synthesis and antimalarial activity of some 2(3H)-furanones bearing quinoline moiety
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A series of substituted 3-[(substituted-2-chloroquinolin-3-yl)methylene]-5- (substituted-phenyl)-furan-2(3H)-ones (4a-p) have been synthesized and evaluated for their in vitro antimalarial activity against P. falciparum. The title compounds were synthesized by condensing 3-(substituted-benzoyl)propionic acids (3a-d) with substituted 2-chloroquinoline-3-carbaldehydes (2a-d) following modified Perkin's reaction. Compounds 3-[2-chloro-6-methylquinolin-3-yl) methylene]-5-(2,4-dimethyl-phenyl)-furan-2(3H)-one (4n) and 3-[2-chloro-6- methoxyquinolin-3-yl)methylene]-5-(2,4-dimethyl-phenyl)-furan-2(3H)-one (4p) showed promising antimalarial activity with MIC of 10 μg/mL.
- Alam, Mohammad Mumtaz,Sarkar, Deba Priya,Alam, Ozair,Husain, Asif,Marella, Akranth,Akhtar, Mymoona,Shaquiquzzaman, Mohammad,Khanna, Suruchi
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p. 231 - 236
(2011/10/09)
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- Synthesis of quinoline-attached furan-2(3H)-ones having anti-inflammatory and antibacterial properties with reduced gastro-intestinal toxicity and lipid peroxidation
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A series of 5-aryl-3-[(2-chloroquinolin-3-yl)methylene] furan-2(3H)- ones (3a-p) were synthesized. The required 3-(substituted benzoyl)propionic acids 2a-d were prepared under Fried?l-Crafts acylation reaction conditions. The substituted 2-chloroquinoline-3-carboxaldehydes 1a-d were synthesized by reaction of substituted phenylethanone oxime with phosphorus oxychloride in presence of dimethylformamide using the Vilsmeier-Haack reaction method. These compounds were screened for their anti-inflammatory and antibacterial activities along with their ulcerogenic and lipid peroxidation potentials. The compounds that showed significant anti-inflammatory activity were further screened for their analgesic activity. The compounds were less toxic in terms of ulcerogenicity as compared to a standard, which was also supported by lipid peroxidation studies. The antibacterial activities were performed against Staphylococcus aureus and Escherichia coli. Compounds 3f, 3n and 3o showed significant activity against both S. aureus and E. coli having an minimum inhibitory concentration (MIC) value of 6.25 μg mL-1. Copyright 2011 (CC) SCS.
- Alam, Mohammad M.,Sarkar, Deba Priya,Husain, Asif,Marella, Akranth,Shaquiquzzaman, Mohammad,Akhter, Mymoona,Shaharyar, Mohammad,Alam, Ozair,Azam, Faizul
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p. 1617 - 1626
(2012/05/05)
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- Synthesis and antimicrobial activity of pyrazolo [3,4-b] quinolines containing pyrimidine moiety
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Various 2-chloroquinoline-3-carbaldehyde-3-(6-p-anisyl-5-cyano-3-N-methyl- 3,4-dihydro pyrimidin-4-one-2-yl) hydrazones4(a-d) have been synthesized by condensation of 6-p-anisyl-5-cyano-2-hydrazino-3-N-methyl-3,4-dihydropyrimidine- 4-one with different 2-chloroquinoline-3-carbaldehydes. The hydrazones on cyclization with DMF/KOH furnished 1-(6-p-anisyl-5-cyano-3-N-methyl-3,4- dihydropyrimidin-4-one-2-yl) pyrazolo [3,4-b] quinolines 5(a-d). All the synthesized compounds were characterized on the basis of IR, 1H NMR and mass spectral data and screened for their antimicrobial activity.
- Joshi,Hallikeri,More, Uttam A.,Basavaraj,Kulkarni
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- Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities
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A simple and regioselective synthesis of 2-chloro-3-formylquinolines through Vilsmeier-Haack cyclisation of N-arylacetamides has been reported. The cyclisation is facilitated by N-arylacetamides bearing electron donating groups at m-position. However, yields of quinolines having electron donating groups are good in all cases. Further, the nucleophilic substitution reaction of the quinolines is also investigated. Similarly, the formyl group in the quinolines is subjected to further transformation into cyano (CAN-NH3) and alkoxycarbonyl (NIS-K2CO3/alcohols) groups to afford corresponding 3-cyano and 3-alkoxycarbonylquinolines, respectively.
- Srivastava, Ambika,Singh
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p. 1868 - 1875
(2007/10/03)
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- NON-PEPTIDE GLP-1 AGONISTS
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Novel non-peptide GLP-1 agonists, pharmaceutical compositions comprising them, use of the non-peptide GLP-1 agonists for the preparation of pharmaceutical compositions and methods for the treatment and/or prevention of disorders and diseases wherein an ac
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Page/Page column 50-51
(2010/02/13)
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- Ultrasonically accelerated vilsmeier haack cyclisation and formylation reactions
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Ultrasonically irradiated Vilsmeier Haack (VH) reaction with acetanilides, hydrocarbons and acetophenones exhibited dramatic rate enhancements with excellent yields. The VH reaction with acetanilides afforded 2-chloro-3-formyl quino-line derivatives, hydrocarbons underwent formylation while hydroxy acetophenones yielded 3-formyl chromones.
- Moazzam Ali, Mir,Sana, Sariah,Tasneem,Rajanna,Saiprakash
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p. 1351 - 1356
(2007/10/03)
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- An efficient and facile synthesis of 2-chloro-3-formyl quinolines from acetanilides in micellar media by Vilsmeier-Haack cyclisation
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Acetanilides efficiently undergo Vilsmeier Haack cyclisation in micellar media to afford 2-chloro-3-formyl quinoline derivatives in good yields. This procedure works efficiently in CTAB (cetyl trimethyl ammonium bromide), SDS (sodium dodecyl sulphate) and TX (Triton-X-100) media under reflux conditions particularly from deactivated acetanilides in good yields.
- Ali,Tasneem,Rajanna,Sai Prakash
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p. 251 - 253
(2007/10/03)
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- Homocamptothecins: Synthesis and antitumor activity of novel E-ring- modified camptothecin analogues
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Homocamptothecin (hCPT), a camptothecin (CPT) analogue with a seven membered β-hydroxylactone which combines enhanced plasma stability and potent topoisomerase I (Topo I) mediated activity, is an attractive template for the elaboration of new anticancer a
- Lavergne, Olivier,Lesueur-Ginot, Laurence,Rodas, Francesc Pla,Kasprzyk, Philip G.,Pommier, Jacques,Demarquay, Danièle,Prévost, Grégoire,Ulibarri, Gérard,Rolland, Alain,Schiano-Liberatore, Anne-Marie,Harnett, Jeremiah,Pons, Dominique,Camara, José,Bigg, Dennis C. H.
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p. 5410 - 5419
(2007/10/03)
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- (1H-tetrazol-5-yl)-2(1H)-quinolinones and-naphthyridones and antiallergic use thereof
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(1H-Tetrazol-5-yl)-2(1H)-quinolones useful as antiallergic agents are described herein. The compounds are prepared by the reaction of sodium azide and ammonium chloride with an appropriate 3-cyano-2(1H)-quinolinone.
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- A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 5. The Synthesis of 2-Chloroquinoline-3-carbaldehydes
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Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution.The reaction is shown to involve successive conversion of the acetanilide into an imidoyl chloride and then an N-(α-chlorovinyl)aniline.The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde.The diformylated intermediates may be isolated in several cases and separately cyclised with polyphosphoric acid.
- Meth-Cohn, Otto,Narine, Bramha,Tarnowski, Brian
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p. 1520 - 1530
(2007/10/02)
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